I tell my clients (and myself) who are in this situation to just drop the receipts in an envelope until the end of the year when they know what their income is and can determine if it is worthwhile to itemize or take standard deduction. Same thing with just about everybody and medical expenses. If you ended up having some catastrophic out of pocket expenses at the end of the year, it would be nice to have a file of receipts for early in the year when you didn't think you would need them.

Another consideration is where you live and how your state tax is figured if you have one. For example, in Oregon you can itemize on the state taxes even if you take standard deduction on federal. Oregon's standard deduction is tiny in comparison. Also, if you are age 62 or older, you can take all of your medical as an itemized deduction on the state return.

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